Finding Himself in Her Ch. 03

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Mr_Owlow
Mr_Owlow
550 Followers

"Can you please try it on for me? If you don't like it we'll change it to something more conservative."

"Well, since you asked so nicely. Oh, you know I can't say no to you!"

"Great! Go to the changing booth and put it on while I find you some heels. Oh, and you can't wear a bra with that dress. What size shoe do you have? A six, six and a half?"

"Umm, I'm a five in male sizes, I don't know if it's the same for girls?"

"I'll check. Now scoot!"

Jaime headed into the dressing room where she stripped down to her panties. Her breasts hung so naturally and felt so real in her hands, especially because the nipple clamp transferred their movement, that they started to feel like a natural part of her body already. She guessed she had to pull the dress on over her head and she was very careful not to smudge her makeup or mess up her hair as she pulled it on.

Kara came into the dressing room as Jaime tried to tie the neckstrap under her hair. Kara helped with the straps and adjusted the dress so the shiny stretchy black fabric draped over Jaime's body in just the right way. It hung loosely over her chest with just a little bit of cleavage, Jaime's perpetually stiff nipples were hinted as she shifted her stance.It was sleeveless and left most of the shoulders bare and showed just a hint of her breasts at the sides. In the back the dress plunged to Jaime's lower back, almost showing her sexy back dimples. The dress was tight over the hips and thighs, showing of Jaime's butt to full effect. The dress ended halfway down the thighs. As Jaime stood admiring herself in the dress Kara knelt down and slipped on a pair of heels on Jaime's small feet. They were a pair of grey sandals with the straps in a crisscross pattern, a four inch stiletto heel and a one inch platform. She knew these were so wrong for someone who had never worn heels but she just fell in love with them and knew they would look terrific with the dress. Kara stepped back and looked Jaime over and said, "Wow, just wow. You are the most beautiful girlfriend I've ever had!"

"Really? That makes me so happy! I feel, I don't know, sexy and really turned on like this. These heels feel really high though."

"I know, but I couldn't resist, they look so hot with that dress. Just keep your shoulders back, chin up and eyes straight ahead, walk with your legs close together and place one foot straight in front of the other like you're walking a tightrope and take shorter steps than you do in low shoes and pants. I'll hold your hand and we can walk around the store for a while until you gain confidence."

Jaime walked around the store, slowly getting more comfortable in the high heels. It was strange to be so much taller, and the heels did something to her posture, she felt somehow more confident, like the proud posture the heels forced her body to take also affected her mindset. They started walking slowly with Kara giving small pointers on how much to move her hips and her posture, but after half the store she felt comfortable enough to walk on her own. She felt the eyes of the few guys in the store on her as well as Kara's hot gaze on her ass as she walked behind her. She loved the click-clack sound the heels made as she walked across the hardwood floor and that it was her heels that was making that sexy sound. Jaime said to Kara, "I love this outfit! I want to wear it out of the store, but I need something for my wallet, cell and keys."

"It looks like it was made for you. Head over to the purses while I get your clothes from the changing room."

As Jaime passed the lingerie on her way to the purses a green satin slip caught her eye, it was dark green and clingy with a beautiful white lace leaf pattern on the top and bottom. It would be great to surprise Kara with tonight. She picked one out in the same size as the dress and headed over to the purses. She picked out a medium sized gray suede handbag that went well with the rest of the outfit and met up with Kara at the counter. The sales girl was very nice and accommodating and Jaime had soon paid and walked out of the store in her new ensemble as her old boy clothes were in a bag in her hand along with her bra and the sexy slip. Kara suggested they head back to her place to freshen up and then out to a bar she loved.

Jaime felt the evening air on her legs all the way up to her panties and on her back and arms. It almost felt like she was walking nude trough the crowded streets and it was extremely exhilarating. The stairs up to Kara's apartment was a new experience, when she was a boy she usually took stairs two steps at a time but now she had to hold on to the rail and take it slowly.

When they reached the apartment Jaime got out of her heels and excused herself to the bathroom. She lifted her dress and pulled down her panties and sat to pee without even thinking about it, it just seemed like the natural thing to do. When she stood up she caught her reflection in the mirror and, having been excited for hours without doing something about it, her cock sprang to attention. The woman in the mirror was gorgeous and Jaime thought she would have been to terrified to approach her as a man. She was a bit uncertain about what to do about the erection, she didn't know if Kara would mind if she masturbated and there was no way she could tuck away this boner. As she stood there Kara knocked on the door and asked, "Sweetie, are you done in there? Let me in, it's just us girls and I need to fix myself up."

"Umm, Okay, but I'm having a dress troubles." Jaime answered and opened the door. Kara's eyes widened at the sight of her and said, "Yes, I can see how that would be a problem in that dress. Lean against that wall and lets see if I can make your trouble go away."

Kara, clad in only a white bra and pantie set, knelt in front of Jaime and pulled her foreskin back with her hand before sucking the big head into her mouth. As she sucked and licked the first three inches one hand jerked off the rest while her other hand fondled Jaime's balls and massaged the rim of her asshole.

It was so incredibly erotic to look down over her own sexy, womanly form to Kara's sweet face eagerly sucking her hard cock that Jaime came into Kara's welcoming mouth after just a few minutes, pulling on her hard nipples and moaning loudly as her body trembled. She kept eye contact with Kara trough the waves of pleasure as her hips bucked uncontrollably. Kara sucked until every drop left her cock and then she stood up and kissed Jaime, feeding Jaime her own cum which she eagerly swallowed. Kara stood back and exclaimed, "Wow! You must really like being a girl! You came really fast."

"Well, yeah. I've been so turned on ever since we put on my breasts and it's strange, but I almost immediately started thinking of myself as a girl. It's like there was something unlocked inside me when I saw myself in that mirror." As Jaime said this she pulled up her panties and tucked away the only parts left of him before pulling the dress down.

Kara responded, "That's wonderful! I think you make a better looking woman than man and I really like that you have a sexy secret tucked away just for me. I bet the attention you got felt good as well?" As she talked she fixed herself up in front of the mirror. Jaime joined her and touched up her lipstick as she answered,

"Well, I think most eyes were on you, you are the most beautiful woman I've ever seen."

Kara beamed at the compliment but said, "Oh, cutie, thank you so much! I'm sure most eyes were on you though, you look incredible in that dress and your new hair style."

Jaime blushed and said, "I think so too. I really liked feeling those eyes on me, I used to feel so invisible but now I was noticed. It really builds your confidence, doesn't it?"

"Yeah, most of the time, but it can get annoying as well. Like when you want to be taken seriously and a guy can't listen or even meet your eyes for long because he keeps staring at your tits. Girls can be just as bad though, but mostly for other reasons, like jealousy. You should be prepared for how catty and vicious girls can be to one another."

"I know. One of my worst bullies was a girl, she was one of the most popular girls in class and was really mean and started rumors about me. Ha, I guess one of them were right." Kara looked questioningly at her and Jaime continued, "Well, she started a rumor about me being a crossdresser and look at me now."

Kara smiled a little smile and said, "I think you are more transsexual, or maybe the hormone thing classifies you as intersexed." Kara pulled Jaime into a hug and continued, "If I had been in your class you would never have been bullied. I don't know if I just want to comfort you or track this bitch down and get some revenge on your behalf."

Jaime smiled a sad little smile and answered, "I like the comforting but there's no need to track her down, I found out later that her parents were really messed up, booze and drugs, and I guess she needed to feel in power somewhere."

"It's incredible how much empathy you have but that still doesn't make it okay. I mean, you've had problems with your parents and you're like the sweetest person ever."

"Thank you. It really doesn't matter anymore, I'm happy now. You said something about going to a bar?"

"Yeah, it's a really nice place, they have live jazz and soul and some good food. I'll just put on some clothes and we'll go. What do you think I should wear, skirt, dress or jeans?"

"Umm, a skirt or dress, because you have such great legs and I haven't seen you in a skirt or dress yet."

Kara agreed and headed to her closet to get dressed as Jaime watched. She picked out a gun metal gray leather skirt that reached her lower thighs, an ivory colored top that contrasted her dark skin nicely and showed off her impressive cleavage and a wide black belt to tie it all together. She put on a necklace of gold and blue sweet water pearls and clasped a similar but green necklace around Jaime's neck. Kara had put on much more dramatic make-up as they talked, dark gold eye shadow and lipstick in the same shade. Kara called a cab to take them to the bar, it was walking distance in regular shoes but in heels like Jaime's or the black stiletto boots she put on herself the cab was necessary.

If walking up the stairs had been difficult then walking down the stairs was damn near impossible. Jaime felt like she would topple forward with every step and clutched desperately to the railing. She had mastered the heels pretty quickly on flat ground but this was another beast all together. When they reached the bottom of the stairs Kara took her hand and led her to the waiting cab. Kara opened the cab door for her and said, "Let's see if you can figure out how to sit down without flashing me or anyone else."

Jaime nodded, she hadn't thought about that problem with her short dress. She turned around and sat down sideways in the seat before she raised both feet with her knees together and swiveled her hips and sat back. Kara gave Jaime a quick thumbs up and went around the car and got in the same way. Kara gave the address and after just ten minutes they were in front of the bar. Jaime got out, careful not to flash her panties at the short cue waiting to get inside. Kara came around and they walked arm in arm to the back of the cue. Jaime saw that everybody was being carded at the entrance and asked Kara in a panicked voice, "What are we going to do? I don't really look like my drivers licence anymore!"

"Calm down, you are not the first t-girl to try passing. I'm sure they will understand, maybe they won't even notice that it says M instead of F. Okay sweetie?

Jaime nodded and took a few deep breaths to calm down. She handed her ID to the gigantic neanderthal bouncer and tried to smile sweetly up at him. The big brute hardly looked at the drivers licence and didn't meet her eyes as his were glued to her cleavage and her permanently hard nipples. Jaime blushed furiously, she wasn't used to being looked at with such lust, and from a man no less. Kara had to tap him on the shoulder to get him to look at her licence and he distractedly waved Jaime by as his attention shifted to Kara's prominent cleavage. After he had a good stare at her lovelies as well he waved them trough.

When they got a few steps away from the bouncer Kara stared in the same bug-eyed way at Jaime's breasts and they both burst out laughing. The laughter felt liberating to Jaime, she had been so tense about passing that she had almost forgotten to breathe. They still had the giggles as they sat down in a booth close to the stage where a live band played 70's soul. Kara reminded Jaime to keep her legs crossed above the knees, unless she wanted to flash her panties at the whole place. A waitress made her way over to their table and gave them menus to look over. Jaime didn't feel that hungry, she ate a big meal after the doctor's visit, so she decided on a chicken salad. She realised that as a girl she could order something fruity and tasty instead of the standard guy drinks; beer, bourbon or whiskey. The waitress came back and took their orders, Kara decided on a chicken salad as well and they ordered Cosmo's while they waited for the food.

Jaime had time to think while she sat and sipped her Cosmo and listened to the great band. She felt more alive than ever since meeting Kara, and even more so since she became a woman. It was an incredible turn on but it went much deeper than that, it felt like she belonged like this, like a woman. She looked around at the people in the bar and caught a few appreciative glances from several men. It was exciting to be seen like this but she felt no attraction what so ever to any of the men, that hadn't changed at least, Jaime was still only attracted to the fairer sex, and especially to the beautiful and strong woman sitting across the table. Jaime reached over and intertwined her fingers with Kara's. She couldn't get over how sexy the contrast between her own pale skin and Kara's caramel hue looked. Kara's hands felt so soft and yet Jaime knew how strong they were and how easily they manipulated her body. The thought of their sexual exploration over the last few days sent a shiver down the short brunette's spine and she felt her well used member stir. It couldn't get far, tucked down under the tight panties and caught between her legs as it was.

Soon after the food came the band ended their set to a big round of applause and lower, recorded music started playing as they ate, so conversation got much easier.

"So, how does it feel to be out and about like this?" Kara asked.

"Well, it's exciting, a bit scary, confusing, but it feels, you know, right." Jaime smiled as she said this and reached over to squeeze Kara's hand again.

Kara downed the last of her Cosmo and asked, "Sweetie, how about you try out this new persona without me by your side? Go to the bar and buy us a couple of drinks."

"Okay, I'll try. Do you want want another Cosmopolitan?"

Kara nodded and watched her bubble butt as Jaime swayed across to the bar. She was amazed at how quickly Jaime had learned to walk in heels, she was a real natural.

Jaime hopped up on a bar stool as she waited for the bartender to make her way over to Jaime's section. She spent her time looking over the different drinks available, she still felt a bit too shy to order a few of the drinks, like a Sex on the Beach or Buttery Nipple and couldn't really understand why someone would come up with those names. Then she saw the drink of the Dude, a White Russian and she knew she had to try it. Just after she ordered she heard the guy to her left say, almost under his breath, "The dude abides."

Jaime giggled looked over at him, she saw that he blushed and replied, "I just wanted my rug back, it really tied the room together!"

The guy laughed out loud and said, "The best movie ever!"

"Yeah, it's my favourite along with Fargo, I've seen both like ten times!" Jaime looked the guy over, he was dressed in a suit and tie and looked to be a lawyer or something.

"Me too! I thought most girls dissed it though? This must be my lucky night, the prettiest girl in here is talking Cohen with me." With that the guy smiled and placed his hand on her arm. Jaime froze for a second as a million thoughts raced through her head and then she relaxed, gently grabbed his wrist and placed it on the bar top and said, "Thanks for the compliment but I'm sorry to burst your bubble, I play for the "other team"."

Suit guy smiled a halfhearted smile and said, "Well, that's just my luck! I knew you were to good to be true."

Jaime got her drinks and said, "Thanks! Just for that I'll tell you that the cute redhead at the end of the bar has been eying you for a while."

Suit guy raised his glass to her with a smile and Jaime did the same before heading back to Kara as suit guy ordered a White Russian for the redhead. After Jaime placed their drinks on the table Kara grabbed hold of her wrist and pulled her onto her lap for a kiss. Jaime lost herself into Kara's welcoming mouth, her universe shrunk down to just Kara and her probing tongue, nothing else mattered. After what could have been a long while or just a few seconds Kara broke the kiss. Jaime moved to get up from her lap but Kara held her back and just shifted them around so that they both sat facing the stage with Jaime resting her head in the crook of Kara's neck. Jaime told Kara about her interaction with suit guy as they sipped their drinks and then a new band came on. Jaime loved the White Russian, it was much better than the Cosmo and would later become her standard drink.

The band played pretty mellow music and several couples danced on the floor in front of the stage. After one more round of drinks Kara and Jaime headed to the dance floor where they danced close, made out and grinded until Jaime was afraid a bulge might show. She was a bit uncertain of how to dance in heels but it helped that Kara took the lead and started slowly. By the end they were so hot and bothered that they rushed out of the bar and hailed a cab, desperate to get to the privacy of Kara's apartment.

As they rode in the backseat of the cab they gave the cabby quite a show. He stared so hard at their make out session that he almost collided with a parked car. Kara felt the taxi swerve and broke the kiss. She needed Jaime badly but not badly enough to risk a car crash. The cab driver smiled apologetically at them through the mirror as they pulled their clothes back into place. Jaime and Kara were both giggly and sat close together holding hands for the rest of the ride. When they arrived Kara paid the cabby and tried to tip him but he said the show was better than any tip.

Jaime felt a bit unsteady as she made her way up the stairs, she had never had this much to drink before and it felt a bit strange. She also felt an urgent need to pee and broke Kara's kissing embrace as they got inside Kara's apartment. Jaime said, "I'm so sorry but I really have to pee!" She tottered into the bathroom as Kara answered, "Okay, I'll slip into something a little more appropriate and you can meet me in the bedroom when you're done."

Jaime pulled her dress up and her panties down and sat down. She sighed with relief and slipped her heels off. As Jaime's bladder voided Kara said through the door, "Sweetie, use one of the fleet thingies before you join me, they're in the cabinet beside the toilet."

"Okay," Jaime answered and opened the door of the cabinet. She found a bottle labeled Fleet Enema and read the instructions. She was a bit surprised at first but then she remembered how great the beads felt and understood that if Kara wanted to play more with her ass then it should be clean. After she was done and stood washing her hands she saw the shopping bags in the mirror and remembered the slip she bought earlier. She shimmied out of her tight black dress and slipped on the green satin slip. The material felt great against her skin and it looked really sexy as her constantly hard fake nipples tented the shiny fabric. The feeling made her cock strain uncomfortably against her thong so she pulled it down, thinking it would come off soon anyway. It was such a relief to let her balls drop and unfurl her stiffening dick that she let out a moan. Her cock lifted the hem of the slip and stood proudly from her feminine form, creating an erotic contrast of male and female.

Mr_Owlow
Mr_Owlow
550 Followers